Carboxamides

ABSTRACT

Use of carboxamides of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which
     A, R 1 , M, Q and R are as defined in the description   for controlling certain rust fungi, such as soya bean rust and coffee rust, in crop protection.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a divisional application of U.S. application Ser.No. 11/916,436, filed Dec. 3, 2007, which is a National Stage filing ofPCT/EP2006/005070, filed May 26, 2006, which claims priority from GermanApplication Number 10 2005 025 989.8 filed Jun. 7, 2005 the contents ofwhich are incorporated by reference in their entireties.

BACKGROUND OF THE INVENTION

1. Field of Invention

The present invention relates to known carboxamides and to their use forcontrolling unwanted microorganisms.

2. Description of Related Art

It is already known that numerous carboxamides have fungicidalproperties (cf., for example, WO 04/103975, WO 04/103953, WO 03/070705,WO 03/010149, WO 02/059086, EP-A 0 824 099, EP-A 0 737 682, EP-A 0 591699, EP-A 0 589 301, EP-A 0 545 099, DE-A 24 09 011, DE-A 20 06 472,JP-A 2001-302605, JP-A 10-251240, JP-A 8-176112, JP-A 8-92223 and JP-A53-72823). Thus, for example, numerous carboxamides and their useagainst Puccinia species, such as, for example, Puccinia recondita, orUromyces species, such as, for example, Uromyces appendiculatus, areknown. The activity of these compounds is good; however, in some cases,for example at low application rates, it is unsatisfactory. It has nowbeen found that these carboxamides are also effective against other rustspecies, such as, for example, soya bean rust, which has only recentlybeen encountered, Phakopsora species, such as, for example, Phakopsorasojae, Phakopsora pachyrhizi, Phakopsora vignae, Uredo sojae, Uromycessojae, but also against other rust species, such as, for example, coffeerust, Helileia vastarix.

SUMMARY OF INVENTION

It has now been found that the carboxamides of the formula (I)

in which

-   A represents optionally substituted aryl or an aromatic or    non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring    having 1 to 3 heteroatoms, which may be O, N or S, where the carbo-    or heterocycle may carry 1, 2 or 3 substituents selected from the    group consisting of alkyl, halogen, haloalkyl, alkylthio,    alkylsulphinyl and alkylsulphonyl,-   R¹ represents hydrogen, C₁-C₈-alkyl, C₁-C₆-alkylsulphinyl,    C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄ alkyl, C₃-C₈-cycloalkyl;    C₁-C₆-haloalkyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃— alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms; (C₁-C₈-alkyl)carbonyl,    (C₁-C₈-alkoxy)carbonyl, (C₁-C₈-alkylthio)carbonyl,    (C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl, (C₃-C₆-alkenyloxy)carbonyl,    (C₃-C₆-alkinyloxy)carbonyl, (C₃-C₈-cycloalkyl)carbonyl;    (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-haloalkoxy)carbonyl,    (C₁-C₆-haloalkylthio)carbonyl,    (halo-C₁-C₄-alkoxy-C₁-C₄-alkyl)carbonyl,    (C₃-C₆-haloalkenyloxy)carbonyl, (C₃-C₆-haloalkinyloxy)carbonyl,    (C₃-C₈-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,    chlorine and/or bromine atoms; or —CH₂—C≡C—R^(1-A),    —CH₂—CH═CH—R^(1-A), —CH═C═CH—R^(1-A), —C(═O)C(═O)R², —CONR³R⁴ or    —CH₂NR⁵R⁶,-   R^(1-A) represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₃-C₇-cycloalkyl,    (C₁-C₄-alkoxy)carbonyl, (C₃-C₆-alkenyloxy)carbonyl,    (C₃-C₆-alkinyloxy)carbonyl or cyano,-   R² represents hydrogen, C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl; C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms,-   R³ and R⁴ independently of one another each represent hydrogen,    C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkyl;    C₁-C₈-haloalkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R³ and R⁴ furthermore together with the nitrogen atom to which they    are attached form a saturated heterocycle which is optionally mono-    or polysubstituted by identical or different substituents from the    group consisting of halogen and C₁-C₄-alkyl and which has 5 to 8    ring atoms, where the heterocycle may contain 1 or 2 further    non-adjacent heteroatoms from the group consisting of oxygen,    sulphur and NR⁷,-   R⁵ and R⁶ independently of one another represent hydrogen,    C₁-C₈-alkyl, C₃-C₈-cycloalkyl; C₁-C₈-haloalkyl, C₃-C₈-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached represent a saturated heterocycle which is optionally    mono- or polysubstituted by identical or different substituents from    the group consisting of halogen and C₁-C₄-alkyl and which has 5 to 8    ring atoms, where the heterocycle may contain 1 or 2 further    non-adjacent heteroatoms from the group consisting of oxygen,    sulphur and NR⁷,-   R⁷ represents hydrogen or C₁-C₆-alkyl,-   M represents a phenyl or thiophene ring, each of which is    monosubstituted by R⁸, or represents substituted C₃-C₆-cycloalkyl or    C₃-C₆-cycloalkenyl, each of which is mono- to tetrasubstituted by    R^(8-B),-   R⁸ represents hydrogen, fluorine, chlorine, methyl, isopropyl,    methylthio or trifluoromethyl,-   R^(8-B) represents hydrogen, fluorine, chlorine, C₁-C₄-alkyl or    C₁-C₄-haloalkyl,-   Q represents a direct bond, C₁-C₄-alkylene, C₂-C₄-alkenylene, O, S,    SO, SO₂ or NR⁹,-   R⁹ represents hydrogen, C₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkinyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkinyl or    C₃-C₆-cycloalkyl,-   R represents in each case optionally substituted phenyl, cycloalkyl    or bicycloalkyl; or represents unsubstituted C₂-C₂₀-alkyl or    represents optionally substituted C₁-C₂₀-alkyl, can be used for    controlling certain rust fungi, such as soya bean rust and coffee    rust, in crop protection.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The compounds of the formula (I) are known.

If appropriate, the carboxamides of the formula (I) can be present asmixtures of various possible isomeric forms, in particularstereoisomers, such as, for example, E and Z, threo and erythro, andalso optical isomers, and, if appropriate, also of tautomers. Theformula (I) includes both the E and the Z isomers, and the threo anderythro and also the optical isomers, any mixtures of these isomers andthe possible tautomeric forms.

The formula (I) provides a general definition of the carboxamides whichcan be used according to the invention. Preferred radical definitionsare given below.

-   A preferably represents one of the radicals A1 to A19 below

in which

-   R¹² represents hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,    C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio having in each case 1 to 5    halogen atoms, aminocarbonyl or aminocarbonyl-C₁-C₄-alkyl,-   R¹³ represents hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy    or C₁-C₄-alkylthio,-   R¹⁴ represents hydrogen, C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl,    C₂-C₆-alkenyl, C₃-C₆-cycloalkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-haloalkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl having    in each case 1 to 5 halogen atoms, or phenyl,-   R¹⁵ and R¹⁶ independently of one another represent hydrogen,    halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms,-   R¹⁷ represents halogen, cyano or C₁-C₄-alkyl, or C₁-C₄-haloalkyl or    C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms,-   R¹⁸ and R¹⁹ independently of one another represent hydrogen,    halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen atoms,-   R²⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R²¹ represents hydrogen, halogen, hydroxyl, cyano, C₁-C₆-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or C₁-C₄-haloalkylthio having in    each case 1 to 5 halogen atoms,-   R²² represents halogen, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio or    C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms,-   R²³ represents hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy having in each    case 1 to 5 halogen atoms, C₁-C₄-alkylsulphinyl or    C₁-C₄-alkylsulphonyl,-   R²⁴ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen    atoms,-   R²⁵ represents C₁-C₄-alkyl,-   Q¹ represents S (sulphur), SO, SO₂ or CH₂,-   P represents 0, 1 or 2, where R²⁵ represents identical or different    radicals if p represents 2,-   R²⁶ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen    atoms,-   R²⁷ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen    atoms,-   R²⁸ and R²⁹ independently of one another represent hydrogen,    halogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen    atoms,-   R³⁰ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R³¹ and R³² independently of one another represent hydrogen,    halogen, amino, nitro, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5    halogen atoms,-   R³³ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R³⁴ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,    di(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1    to 5 halogen atoms,-   R³⁵ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5    halogen atoms,-   R³⁶ represents hydrogen, halogen, amino, C₁-C₄-alkylamino,    di(C₁-C₄-alkyl)amino, cyano, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1    to 5 halogen atoms,-   R³⁷ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5    halogen atoms,-   R³⁸ represents halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5    halogen atoms,-   R³⁹ represents hydrogen or C₁-C₄-alkyl,-   R⁴⁰ represents halogen or C₁-C₄-alkyl,-   R⁴¹ represents C₁-C₄-alkyl or C₁-C₄-haloalkyl having 1 to 5 halogen    atoms,-   R⁴² represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R⁴³ represents halogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkylthio or    C₁-C₄-haloalkoxy having in each case 1 to 5 halogen atoms,-   R⁴⁴ represents hydrogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl having    1 to 5 halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl,    C₁-C₄-alkylsulphonyl, di(C₁-C₄-alkyl)aminosulphonyl,    C₁-C₆-alkylcarbonyl or in each case optionally substituted    phenylsulphonyl or benzoyl,-   R⁴⁵ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R⁴⁶ represents hydrogen, halogen, cyano, C₁-C₄-alkyl or    C₁-C₄-haloalkyl having 1 to 5 halogen atoms,-   R⁴⁷ represents hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl    having 1 to 5 halogen atoms,-   R⁴⁸ represents C₁-C₄-alkyl.-   A particularly preferably represents one of the radicals A1, A2, A3,    A4, A5, A6, A9, A10, A11, A12, A17 or A18.-   A very particularly preferably represents one of the radicals    -   A1, A2, A4, A5, A6, A9, All, A16, A17, A18.-   A especially preferably represents the radical A1.-   A furthermore especially preferably represents the radical A2.-   A furthermore especially preferably represents the radical A4.-   A furthermore especially preferably represents the radical A5.-   A furthermore especially preferably represents the radical A6.-   A furthermore especially preferably represents the radical A9.-   A furthermore especially preferably represents the radical A11.-   A furthermore especially preferably represents the radical A16.-   A furthermore especially preferably represents the radical A18.-   R¹ preferably represents hydrogen, C₁-C₆-alkyl,    C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,    C₁-C₄-haloalkylsulphonyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃-C₈-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms; formyl, formyl-C₁-C₃-alkyl,    (C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl;    halo-(C₁-C₃-alkyl)carbonyl-C₁-C₃-alkyl,    halo-(C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkyl having in each case 1 to 13    fluorine, chlorine and/or bromine atoms; (C₁-C₆-alkyl)carbonyl,    (C₁-C₄-alkoxy)carbonyl, (C₁-C₄-alkylthio)carbonyl,    (C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl, (C₃-C₄-alkenyloxy)carbonyl,    (C₃-C₄-alkinyloxy)carbonyl, (C₃-C₆-cycloalkyl)carbonyl;    (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-haloalkoxy)carbonyl,    (C₁-C₄-haloalkylthio)carbonyl,    (halo-C₁-C₃-alkoxy-C₁-C₃-alkyl)carbonyl,    (C₃-C₄-haloalkenyloxy)carbonyl, (C₃-C₄-haloalkinyloxy)carbonyl,    (C₃-C₆-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine,    chlorine and/or bromine atoms; or —CH₂—C≡C—R^(1-A),    —CH₂—CH═CH—R^(1-A), —CH═C═CH—R^(1-A), —C(═O)C(═O)R², —CONR³R⁴ or    —CH₂NR⁵R⁶.-   R¹ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl,    methylsulphinyl, ethylsulphinyl, n- or isopropylsulphinyl, n-, iso-,    sec- or tert-butylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    isopropylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl,    methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl,    trifluoroethyl, difluoromethylthio, difluorochloromethylthio,    trifluoromethylthio, trifluoromethylsulphinyl,    trifluoromethylsulphonyl, trifluoromethoxymethyl; formyl, —CH₂—CHO,    —(CH₂)₂—CHO, —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂,    —(CH₂)₂—CO—CH₃, —(CH₂)₂—CO—CH₂CH₃, —(CH₂)₂—CO—CH(CH₃)₂, —CH₂—CO₂CH₃,    —CH₂—CO₂CH₂CH₃, —CH₂—CO₂CH(CH₃)₂, —(CH₂)₂—CO₂CH₃, —(CH₂)₂—CO₂CH₂CH₃,    —(CH₂)₂—CO₂CH(CH₃)₂, —CH₂—CO—CF₃, —CH₂—CO—CCl₃, —CH₂—CO—CH₂CF₃,    —CH₂—CO—CH₂CCl₃, —(CH₂)₂—CO—CH₂CF₃, —(CH₂)₂—CO—CH₂CCl₃,    —CH₂—CO₂CH₂CF₃, —CH₂—CO₂CF₂CF₃, —CH₂—CO₂CH₂CCl₃, —CH₂—CO₂CCl₂CCl₃,    —(CH₂)₂—CO₂CH₂CF₃, —(CH₂)₂—CO₂CF₂CF₃, —(CH₂)₂—CO₂CH₂CCl₃,    —(CH₂)₂—CO₂CCl₂CCl₃; methylcarbonyl, ethylcarbonyl,    n-propylcarbonyl, isopropylcarbonyl, tert-butylcarbonyl,    methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl,    tert-butoxycarbonyl, methylthiocarbonyl, ethylthiocarbonyl, is    opropylthiocarbonyl, tert-butylthiocarbonyl, methoxymethylcarbonyl,    ethoxymethylcarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl,    trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, or    —CH₂—C≡C—R^(1-A), —CH₂—CH═CH—R^(1-A), —CH═C═CH—R^(1-A),    —C(═O)C(═O)R², —CONR³R⁴ or —CH₂NR⁵R⁶.-   R¹ very particularly preferably represents hydrogen, methyl,    methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl,    —CH₂—C≡CH, —CH₂—CH═CH₂, —CH═C═CH₂, —CH₂—CHO, —(CH₂)₂—CHO,    —CH₂—CO—CH₃, —CH₂—CO—CH₂CH₃, —CH₂—CO—CH(CH₃)₂, —C(═O)CHO,    —C(═O)C(═O)CH₃, —C(═O)C(═O)CH₂OCH₃, —C(═O)CO₂CH₃, —C(═O)CO₂CH₂CH₃.-   R^(1-A) preferably represents hydrogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkinyl, C₃-C₆-cycloalkyl,    (C₁-C₄-alkoxy)carbonyl or cyano.-   R^(1-A) particularly preferably represents hydrogen, methyl or    ethyl.-   R² preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-alkoxy,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cyclo alkyl; C₁-C₄-halo alkyl,    C₁-C₄-halo alkoxy, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl,    C₃₋₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R² particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, tert-butyl, methoxy, ethoxy, n- or isopropoxy,    tert-butoxy, methoxymethyl, cyclopropyl; trifluoromethyl,    trifluoromethoxy.-   R³ and R⁴ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl;    C₁-C₄-haloalkyl, halo-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-halocycloalkyl    having in each case 1 to 9 fluorine, chlorine and/or bromine atoms.-   R³ and R⁴ furthermore together with the nitrogen atom to which they    are attached preferably form a saturated heterocycle which is    optionally mono- to tetrasubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl    and which has 5 or 6 ring atoms, where the heterocycle may contain 1    or 2 further non-adjacent heteroatoms from the group consisting of    oxygen, sulphur and NR⁷.

R³ and R⁴ independently of one another particularly preferably representhydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl,cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl,trifluoroethyl, trifluoromethoxymethyl.

-   R³ and R⁴ furthermore together with the nitrogen atom to which they    are attached particularly preferably form a saturated heterocycle    from the group consisting of morpholine, thiomorpholine and    piperazine, where the piperazine may be substituted on a second    nitrogen atom by R⁷, each of which radical is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and methyl.-   R⁵ and R⁶ independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl; C₁-C₄-haloalkyl,    C₃-C₆-halocycloalkyl having in each case 1 to 9 fluorine, chlorine    and/or bromine atoms.-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached preferably form a saturated heterocycle which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₄-alkyl    and which has 5 or 6 ring atoms, where the heterocycle may contain 1    or 2 further non-adjacent heteroatoms from the group consisting of    oxygen, sulphur and NR⁷.-   R⁵ and R⁶ independently of one another particularly preferably    represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-    or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,    ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl,    trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.-   R⁵ and R⁶ furthermore together with the nitrogen atom to which they    are attached particularly preferably form a saturated heterocycle    from the group consisting of morpholine, thiomorpholine and    piperazine, where the piperazine may be substituted on a second    nitrogen atom by R⁷, each of which radical is optionally mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine and methyl.-   R⁷ preferably represents hydrogen or C₁-C₄-alkyl.-   R⁷ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, iso-, sec- or tert-butyl.-   M preferably represents one of the cycles below

where the bond marked “*” is attached to the amide.

-   M Particularly preferably represents a ring selected from the group    consisting of M-1, M-7, M-12, M-14, M-15 or M-17.-   M very particularly preferably represents the ring M-1.-   M furthermore very particularly preferably represents the ring M-7.-   M furthermore very particularly preferably represents the ring M-12.-   M furthermore very particularly preferably represents the ring M-14.-   M furthermore very particularly preferably represents the ring M-15.-   M furthermore very particularly preferably represents the ring M-17.-   m represents 0, 1 or 2.-   n represents 0, 1, 2, 3 or 4.-   r represents 0 or 1.-   R⁸ preferably represents hydrogen.-   R⁸, if M represents M-1, furthermore preferably represents fluorine,    where fluorine is particularly preferably in the 4-, 5- or    6-position, very particularly preferably in the 4- or 6-position,    especially in the 4-position.-   R⁸ if M represents M-1, furthermore preferably represents chlorine,    where chlorine is particularly preferably in the 4- or 6-position.-   R⁸, if M represents M-1, furthermore preferably represents methyl,    where methyl is particularly preferably in the 3-position.-   R⁸, if M represents M-1, furthermore preferably represents    trifluoromethyl, where trifluoromethyl is particularly preferably in    the 4- or 6-position.-   R⁸, if M represents M-2, M-3, M-4 or M-5, furthermore preferably    represents fluorine, where fluorine is particularly preferably in    the 6-position (M-2, M-3) or in the 3-position (M-4, M-5).-   R⁸, if M represents M-2, M-3, M-4 or M-5, furthermore preferably    represents chlorine, where chlorine is particularly preferably in    the 6-position (M−2, M-3) or in the 3-position (M-4, M-5).-   R⁸, if M represents M-2, M-3, M-4 or M-5, furthermore preferably    represents methyl, where methyl is particularly preferably in the    4-position (M-2) or in the 3-position (M-3, M-4, M-5).-   R⁸, if M represents M-6, furthermore preferably represents methyl,    where methyl is particularly preferably in the 3-position.-   R⁸, if M represents M-6, furthermore preferably represents    trifluoromethyl, where trifluoromethyl is particularly preferably in    the 3-position.-   R⁸, if M represents M-7, M-8 or M-9, furthermore preferably    represents chlorine, where chlorine is particularly preferably in    the 5-position (M-7, M-8) or in the 3-position (M-9).-   R⁸, if M represents M-7, M-8 or M-9, furthermore preferably    represents methyl, where methyl is particularly preferably in the    5-position (M-7, M-8) or in the 3-position (M-9).-   R^(8-B) preferably represents fluorine, chlorine, methyl, ethyl, n-    or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl or    difluoromethyl, where the radicals R^(8-B) may be identical or    different if m or n is greater than 1.-   Q preferably represents a direct bond.-   Q furthermore preferably represents —CH₂—, —(CH₂)₂—, —(CH₂)₃—,    —CH(CH₃)—, —C(CH₃)₂—, particularly preferably represents —CH₂—,    —(CH₂)₂—, —CH(CH₃)—.-   Q furthermore preferably represents —CH═CH—, —CH₂—CH═CH—,    —CH(CH₃)—CH═CH—, particularly preferably represents —CH═CH—,    —CH₂—CH═CH—.-   Q furthermore preferably represents O.-   Q furthermore preferably represents S.-   Q furthermore preferably represents SO.-   Q furthermore preferably represents SO₂.-   Q furthermore preferably represents NR⁹, particularly preferably    represents NH.-   R⁹ preferably represents hydrogen, C₁-C₆-alkyl,    C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₃-alkylthio-C₁-C₃-alkyl or    C₃-C₆-cycloalkyl.-   R⁹ particularly preferably represents hydrogen, methyl, ethyl, n- or    isopropyl, n-, sec-, iso- or tert-butyl, methoxymethyl,    ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl,    ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl.-   R⁹ very particularly preferably represents hydrogen, methyl, ethyl,    n- or isopropyl, iso- or tert-butyl, methoxymethyl or    methylthiomethyl.-   R preferably represents phenyl which is optionally mono- to    pentasubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   R particularly preferably represents monosubstituted phenyl, where    the substituents are selected from the list W¹.-   R also particularly preferably represents phenyl which is    disubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   R also particularly preferably represents phenyl which is    trisubstituted by identical or different substituents, where the    substituents are selected from the list W¹.-   R very particularly preferably represents phenyl which is    monosubstituted in the 4-position, where the substituents are    selected from the list W¹.-   R very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    3,4-position, where the substituents are selected from the list W¹.-   R very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    2,4-position, where the substituents are selected from the list W¹.-   R very particularly preferably represents phenyl which is    disubstituted by identical or different substituents in the    3,5-position, where the substituents are selected from the list W¹.-   R very particularly preferably represents phenyl which is    trisubstituted by identical or different substituents in the    2,4,6-position, where the substituents are selected from the list    W¹.-   W¹ represents halogen, cyano, nitro, amino, hydroxyl, formyl,    carboxyl, carbamoyl, thiocarbamoyl; in each case straight-chain or    branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl,    alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or    alkylsulphonyl having in each case 1 to 8 carbon atoms;    -   in each case straight-chain or branched alkenyl or alkenyloxy        having in each case 2 to 6 carbon atoms;    -   in each case straight-chain or branched haloalkyl, haloalkoxy,        haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl having        in each case 1 to 6 carbon atoms and 1 to 13 identical or        different halogen atoms;    -   in each case straight-chain or branched haloalkenyl or        haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to        11 identical or different halogen atoms;    -   in each case straight-chain or branched alkylamino,        dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl,        alkylaminocarbonyl, dialkylaminocarbonyl,        arylalkylaminocarbonyl, dialkylaminocarbonyloxy having 1 to 6        carbon atoms in the respective hydrocarbon chains,        alkenylcarbonyl or alkinylcarbonyl having 2 to 6 carbon atoms in        the respective hydrocarbon chains;    -   cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon        atoms;    -   in each case doubly attached alkylene having 3 or 4 carbon        atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene        having 1 or 2 carbon atoms, each of which radical is optionally        mono- to tetrasubstituted by identical or different substituents        from the group consisting of fluorine, chlorine, oxo, methyl,        trifluoromethyl and ethyl;    -   or a grouping —C(Q¹)═N-Q², in which    -   Q¹ represents hydrogen, hydroxyl, alkyl having 1 to 4 carbon        atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical        or different halogen atoms or cycloalkyl having 1 to 6 carbon        atoms and    -   Q² represents hydroxyl, amino, methylamino, phenyl, benzyl or        represents in each case optionally halogen-, cyano-, hydroxyl-,        alkoxy-, alkylthio-, alkylamino-, dialkylamino- or        phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms,        or represents alkenyloxy or alkinyloxy having in each case 2 to        4 carbon atoms,        and also phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,        cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy,        phenylalkylthio or heterocyclylalkyl having in each case 1 to 3        carbon atoms in the respective alkyl moieties, each of which        radical is optionally mono- to trisubstituted in the cyclic part        by halogen and/or straight-chain or branched alkyl or alkoxy        having 1 to 4 carbon atoms.-   W¹ preferably represents fluorine, chlorine, bromine, methyl, ethyl,    n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n-    or isopropoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy,    trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, in each    case doubly attached difluoromethylenedioxy or    tetrafluoroethylenedioxy, or a grouping —C(Q¹)═N-Q², in which-   Q¹ represents hydrogen, methyl, ethyl, trifluoromethyl or    cyclopropyl and-   Q² represents hydroxyl, methoxy, ethoxy, propoxy or isopropoxy.-   R furthermore preferably represents cycloalkyl or bicycloalkyl, each    of which is optionally mono- to tetrasubstituted by identical or    different substituents from the group consisting of C₁-C₄-alkyl and    each of which has 3 to 10 carbon atoms.-   R furthermore particularly preferably represents cyclopentyl,    cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl,    bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl.-   R furthermore preferably represents unsubstituted C₂-C₂₀-alkyl or    represents C₁-C₂₀-alkyl which is mono- or polysubstituted by    identical or different substituents from the group consisting of    fluorine, chlorine, bromine, iodine and/or C₃-C₆-cycloalkyl, where    the cycloalkyl moiety for its part may optionally be mono- to    tetrasubstituted by identical or different substituents from the    group consisting of fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl    and C₁-C₄-haloalkyl.-   R furthermore particularly preferably represents unsubstituted    C₂-C₂₀-alkyl.-   R furthermore particularly preferably represents C₁-C₂₀-alkyl which    is substituted by chlorine, cyclopropyl, dichlorocyclopropyl,    cyclobutyl, cyclopentyl or cyclohexyl.-   R¹² preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy,    methylthio, ethylthio, cyclopropyl, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine    and/or bromine atoms, trifluoromethylthio, difluoromethylthio,    aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl.-   R¹² particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl,    monofluoroethyl, difluoromethyl, trifluoromethyl,    difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl,    methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio,    ethylthio, trifluoromethylthio or difluoromethylthio.-   R¹² very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl,    monofluoroethyl, difluoromethyl, trifluoromethyl,    difluorochloromethyl or trichloromethyl.-   R¹² especially preferably represents methyl, difluoromethyl,    trifluoromethyl or 1-fluoroethyl.-   R¹³ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.-   R¹³ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine or methyl.-   R¹³ very particularly preferably represents hydrogen, fluorine,    chlorine or methyl.-   R¹⁴ preferably represents hydrogen, methyl, ethyl, n-propyl,    isopropyl, C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or    bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl,    cyclopentyl, cyclohexyl or phenyl.-   R¹⁴ particularly preferably represents hydrogen, methyl, ethyl,    isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl,    hydroxyethyl or phenyl.-   R¹⁴ very particularly preferably represents hydrogen, methyl,    trifluoromethyl or phenyl.-   R¹⁴ especially preferably represents methyl.-   R¹⁵ and R¹⁶ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R¹⁵ and R¹⁶ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, difluorochloromethyl or    trichloromethyl.-   R¹⁵ and R¹⁶ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.-   R¹⁵ and R¹⁶ especially preferably each represent hydrogen.-   R¹⁷ preferably represents fluorine, chlorine, bromine, cyano,    methyl, ethyl, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in each    case 1 to 5 fluorine, chlorine and/or bromine atoms.-   R¹⁷ particularly preferably represents fluorine, chlorine, bromine,    cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy,    difluorochloromethoxy or trichloromethoxy.-   R¹⁷ very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.-   R¹⁷ especially preferably represents methyl.-   R¹⁷ especially preferably represents trifluoromethyl.-   R¹⁸ and R¹⁹ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R¹⁸ and R¹⁹ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, difluorochloromethyl or    trichloromethyl.-   R¹⁸ and R¹⁹ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.-   R¹⁸ and R¹⁹ especially preferably each represent hydrogen.-   R²⁰ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R²⁰ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl or trifluoromethyl.-   R²⁰ very particularly preferably represents methyl.-   R²⁰ especially preferably represents trifluoromethyl.-   R²¹ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, hydroxyl, cyano, C₁-C₄-alkyl, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy or C₁-C₂-haloalkylthio having in each case 1 to 5    fluorine, chlorine and/or bromine atoms.-   R²¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl,    isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl,    trifluoromethyl, difluorochloromethyl, trichloromethyl,    trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,    trichloromethoxy, trifluoromethylthio, difluoromethylthio,    difluorochloromethylthio or trichloromethylthio.-   R²¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl    or trichloromethyl.-   R²¹ especially preferably represents iodine, methyl, difluoromethyl    or trifluoromethyl.-   R²² preferably represents fluorine, chlorine, bromine, iodine,    hydroxyl, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio,    ethylthio, difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl    or C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R²² particularly preferably represents fluorine, chlorine, bromine,    iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl,    difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy,    ethoxy, methylthio, ethylthio, difluoromethylthio,    trifluoromethylthio, trifluoromethoxy, difluoromethoxy,    difluorochloromethoxy or trichloromethoxy.-   R²² very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R²³ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, cyano, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,    C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy having in each case 1 to 5    fluorine, chlorine and/or bromine atoms, C₁-C₂-alkylsulphinyl or    C₁-C₂-alkylsulphonyl.-   R²³ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio,    ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy,    trichloromethoxy, methylsulphinyl or methylsulphonyl.-   R²³ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    trichloromethyl, methylsulphinyl or methylsulphonyl.-   R²³ especially preferably represents hydrogen.-   R²⁴ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R²⁴ particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁵ preferably represents methyl or ethyl.-   R²⁵ particularly preferably represents methyl.-   Q¹ preferably represents S (sulphur), SO₂ or CH₂.-   Q¹ particularly preferably represents S (sulphur) or CH₂.-   Q¹ very particularly preferably represents S (sulphur).-   p preferably represents 0 or 1.-   p Particularly preferably represents 0.-   R²⁶ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R²⁶ particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁶ very particularly preferably represents methyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R²⁷ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R²⁷ particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁷ very particularly preferably represents methyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R²⁸ and R²⁹ independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or    C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R²⁸ and R²⁹ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R²⁸ and R²⁹ independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R²⁸ and R²⁹ especially preferably each represent hydrogen.-   R³⁰ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine,    chlorine and/or bromine atoms.-   R³⁰ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl or trichloromethyl.-   R³⁰ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl    or trichloromethyl.-   R³⁰ especially preferably represents methyl.-   R³¹ and R³² independently of one another preferably represent    hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³¹ and R³² independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, nitro, methyl,    ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³¹ and R³² independently of one another very particularly    preferably represent hydrogen, fluorine, chlorine, bromine, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R³¹ and R³² especially preferably each represent hydrogen.-   R³³ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R³³ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl, ethyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl or trichloromethyl.-   R³³ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R³³ especially preferably represents methyl.-   R³⁴ preferably represents hydrogen, fluorine, chlorine, bromine,    amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁴ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³⁴ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, amino, methylamino, dimethylamino, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁴ especially preferably represents amino, methylamino,    dimethylamino, methyl or trifluoromethyl.-   R³⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁵ particularly preferably represents fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl    or trichloromethyl.-   R³⁵ very particularly preferably represents fluorine, chlorine,    bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁵ especially preferably represents methyl, trifluoromethyl or    difluoromethyl.-   R³⁶ preferably represents hydrogen, fluorine, chlorine, bromine,    amino, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, cyano, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁶ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R³⁶ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, amino, methylamino, dimethylamino, methyl,    trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁶ especially preferably represents amino, methylamino,    dimethylamino, methyl or trifluoromethyl.-   R³⁷ preferably represents fluorine, chlorine, bromine, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁷ particularly preferably represents fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl    or trichloromethyl.-   R³⁷ very particularly preferably represents fluorine, chlorine,    bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁷ especially preferably represents methyl, trifluoromethyl or    difluoromethyl.-   R³⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl    or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine and/or bromine    atoms.-   R³⁸ particularly preferably represents fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl    or trichloromethyl.-   R³⁸ very particularly preferably represents fluorine, chlorine,    bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.-   R³⁹ preferably represents hydrogen, methyl or ethyl.-   R³⁹ particularly preferably represents methyl.-   R⁴⁰ preferably represents fluorine, chlorine, bromine, methyl or    ethyl.-   R⁴⁰ particularly preferably represents fluorine, chlorine or methyl.-   R⁴¹ preferably represents methyl, ethyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R⁴¹ particularly preferably represents methyl, ethyl,    trifluoromethyl, difluoromethyl, difluorochloromethyl or    trichloromethyl.-   R⁴¹ very particularly preferably represents methyl, trifluoromethyl,    difluoromethyl or trichloromethyl.-   R⁴¹ especially preferably represents methyl or trifluoromethyl.-   R⁴² preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R⁴² particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl or trifluoromethyl.-   R⁴³ preferably represents fluorine, chlorine, bromine, iodine,    hydroxyl, C₁-C₄-alkyl, methoxy, ethoxy, methylthio, ethylthio,    difluoromethylthio, trifluoromethylthio, C₁-C₂-haloalkyl or    C₁-C₂-haloalkoxy having in each case 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R⁴³ particularly preferably represents fluorine, chlorine, bromine,    iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,    sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl,    difluorochloromethyl or trichloromethyl.-   R⁴³ very particularly preferably represents fluorine, chlorine,    bromine, iodine, methyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R⁴⁴ preferably represents hydrogen, methyl, ethyl, C₁-C₂-haloalkyl    having 1 to 5 fluorine, chlorine and/or bromine atoms,    C₁-C₂-alkoxy-C₁-C₂-alkyl, hydroxymethyl, hydroxyethyl,    methylsulphonyl or dimethylaminosulphonyl.-   R⁴⁴ particularly preferably represents hydrogen, methyl, ethyl,    trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or    hydroxyethyl.-   R⁴⁴ very particularly preferably represents methyl or methoxymethyl.-   R⁴⁵ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R⁴⁵ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or    trichloromethyl.-   R⁴⁵ very particularly preferably represents hydrogen or methyl.-   R⁴⁶ preferably represents hydrogen, fluorine, chlorine, bromine,    iodine, cyano, methyl, ethyl, isopropyl or C₁-C₂-haloalkyl having 1    to 5 fluorine, chlorine and/or bromine atoms.-   R⁴⁶ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl,    difluoromethyl, difluorochloromethyl or trichloromethyl.-   R⁴⁶ very particularly preferably represents hydrogen, methyl,    difluoromethyl or trifluoromethyl.-   R⁴⁷ preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl or C₁-C₂-haloalkyl having 1 to 5 fluorine, chlorine    and/or bromine atoms.-   R⁴⁷ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl or trifluoromethyl.-   R⁴⁷ very particularly preferably represents hydrogen.-   R⁴⁸ preferably represents methyl, ethyl, n-propyl or isopropyl.-   R⁴⁸ particularly preferably represents methyl or ethyl.

Preference is given to those compounds of the formula (I) in which allradicals each have the preferred meanings mentioned above.

Particular preference is given to those compounds of the formula (I) inwhich all radicals each have the particularly preferred meaningsmentioned above.

Compounds of the formula (I) which are emphasized are those mentionedbelow:

-   (1)    N-[2-(1,3-dimethylbutyl)phenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide    (known from JP-A 10-251240) of the formula

-   (2)    N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide    (known from WO 03/010149) of the formula

-   (3)    N-[2-(1,3-dimethylbutyl)phenyl]-5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxamide    (known from JP-A 10-251240) of the formula

-   (4)    3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide    of the formula

-   (5)    3-(trifluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 2004/067515) of the formula

-   (6)    3-(trifluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-5-chloro-1-methyl-1H-pyrazole-4-carboxamide    (known from JP-A 10-251240) of the formula

-   (7)    1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    of the formula

-   (8)    5-fluoro-1,3-dimethyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    (known from WO 03/010149) of the formula

-   (9)    3-(difluoromethyl)-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    of the formula

-   (10)    3-(trifluoromethyl)-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    of the formula

-   (11)    3-(trifluoromethyl)-5-fluoro-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    (known from WO 2004/067515) of the formula

-   (12)    3-(trifluoromethyl)-5-chloro-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-1H-pyrazole-4-carboxamide    of the formula

-   (13) N-[2-(1,3-dimethylbutyl)phenyl]-2-iodobenzamide (known from WO    2004/005242) of the formula

-   (14) 2-iodo-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide (known from    WO 2004/005242) of the formula

-   (15) N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide    (known from WO 2004/005242) of the formula

-   (16) 2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide    (known from WO 2004/005242) of the formula

-   (17) boscalid (known from DE-A 195 31 813) of the formula

-   (18)    N-(3-p-tolylthiophen-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide    (known from EP-A 0 737 682) of the formula

-   (19) penthiopyrad (known from EP-A 0 737 682) of the formula

-   (20)    N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide    (known from WO 02/38542) of the formula

-   (21)    N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 03/070705) of the formula

-   (22)    3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 02/08197) of the formula

-   (23)    3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 02/08197) of the formula

-   (24)    N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide    (known from WO 00/14701) of the formula

-   (25)    N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carb    oxamide (known from WO 03/066609) of the formula

-   (26)    N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (27)    N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (28)    4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (29)    N-(4′-iodo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (30)    N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(difluoromethyl)-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (31) tiadinil (known from U.S. Pat. No. 6,616,054) of the formula

-   (32)    N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide    (known from WO 02/38542) of the formula

-   (33)    N-(4′-chlorobiphenyl-2-yl)-3-iodo-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 2004/103975) of the formula

-   (34)    4-(difluoromethyl)-N-[3′-fluoro-4′-(trifluoromethyl)biphenyl-2-yl]-2-methyl-1,3-thiazole-5-carboxamide    (known from WO 03/066610) of the formula

-   (35)    3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 2005/042494) of the formula

-   (36)    N-[2-(3,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide    (known from WO 2005/042494) of the formula

-   (37)    N-[3′-fluoro-4′-(trifluoromethyl)biphenyl-2-yl]-3-iodo-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 2004/103975) of the formula

-   (38)    3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)-4-fluorophenyl]-1-methyl-1H-pyrazole-4-carboxamide    (known from WO 2005/042492) of the formula

-   (39)    4-(difluoromethyl)-2-methyl-N-{2-[2-(trimethylsilyl)ethyl]-3-thienyl}-1,3-thiazole-5-carboxamide

Emphasis is given to compounds of the formula (I) in which R¹ representshydrogen. Emphasis is given to compounds of the formula (I) in which R¹represents formyl. Emphasis is furthermore given to compounds of theformula (I) in which R¹ represents —C(═O)C(═O)R², where R² is as definedabove.

The definition C₁-C₂₀-alkyl comprises the largest range defined here foran alkyl radical. Specifically, this definition comprises the meaningsmethyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl, and in eachcase all isomeric pentyls, hexyls, heptyls, octyls, nonyls, decyls,undecyls, dodecyls, tridecyls, tetradecyls, pentadecyls, hexadecyls,heptadecyls, octadecyls, nonadecyls and eicosyls. Among these,preference is given to the meanings methyl, ethyl, n-, isopropyl, n-,iso-, sec-, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl,1-methylpentyl, 4-methylpentyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl,1,2,2-trimethylpropyl, n-heptyl, 1-methylhexyl, 5-methylhexyl,1,4-dimethylpentyl, 4,4-dimethylpentyl, 1,3,3-trimethylbutyl,1,2,3-trimethylbutyl.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy. Doubly attached hydrocarbon radicals, such asalkylene (alkanediyl), can also in each case be straight-chain orbranched as far as this is possible.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitutions the substituents can be identical ordifferent. Thus, the definition dialkylamino also includes an aminogroup which is substituted asymmetrically by alkyl, such as, forexample, methylethylamino.

Halogen-substituted radicals, such as, for example, haloalkyl, are mono-or polyhalogenated. In the case of polyhalogenation, the halogen atomscan be identical or different. Here, halogen represents fluorine,chlorine, bromine and iodine, in particular fluorine, chlorine andbromine

The general or preferred radical definitions or illustrations givenabove can be combined between the respective ranges and preferred rangesas desired. The definitions apply both to the end products and,correspondingly, to precursors and intermediates.

The compounds according to the invention have strong microbicidal actionand can be used for controlling certain rust fungi, such as soya beanrust and coffee rust, in crop protection.

The following diseases of soya plants can preferably be controlled:

alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose(Colletotrichum gloeosporoides dematium var. truncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostictasojaecola), powdery mildew (Microsphaera diffusa), pyrenochaeta leafspot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and webblight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), scab(Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum),target spot (Corynespora cassiicola), black root rot (Calonectriacrotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight orwilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusariumorthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscusroot rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopsporavasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker(Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthoramegasperma), brown stem rot (Phialophora gregata), pythium rot (Pythiumaphanidermatum, Pythium irregulare, Pythium debaryanum, Pythiummyriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, anddamping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotiniasclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii),thielaviopsis root rot (Thielaviopsis basicola). Particular preferenceis given to using the carboxamides of the formula (I) for controllingPhakopsora pachyrhizi.

In the present case, unwanted microorganisms are to be understood asmeaning the organisms mentioned above. The compounds according to theinvention can therefore be employed for protecting plants against attackby the abovementioned pathogens within a certain period of time afterthe treatment. The period of time within which protection is effectedgenerally extends from 1 to 10 days, preferably from 1 to 7 days, afterthe treatment of the plants with the active compounds.

The fact that the active compounds, in the concentrations required forcontrolling plant diseases, are well tolerated by plants permits thetreatment of above-ground parts of plants, of vegetative propagationmaterial and seed, and of the soil.

In this context, the carboxamides of the formula (I) can be used withparticularly good results for controlling soya bean diseases, such as,for example, against Phakopsora species.

The carboxamides of the formula (I) are also suitable for increasing theyield. Moreover, they display a low degree of toxicity and are toleratedwell by plants.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood as meaning, in the present context, allplants and plant populations, such as desired and undesired wild plantsor crop plants (including naturally occurring crop plants). Crop plantsmay be plants which can be obtained by conventional breeding andoptimization methods or else by biotechnological and genetic engineeringmethods or by combinations of these methods, including the transgenicplants and including the plant varieties capable or not capable of beingprotected by plant breeders' rights. Plant parts are to be understood asmeaning all above-ground and subterranean parts and organs of theplants, such as shoot, leaf, flower and root, examples which may bementioned being leaves, needles, stalks, stems, flowers, fruitingbodies, fruits and seeds, and also roots, tubers and rhizomes. The plantparts also include harvested material and vegetative and generativepropagation material, for example cuttings, tubers, rhizomes, slips andseeds.

The treatment according to the invention with the active compounds, ofthe plants and plant parts, is carried out directly or by acting ontheir environment, habitat, or store by the customary treatment methods,for example by immersion, spraying, vaporizing, fogging, broadcasting,painting on and, in the case of propagation material, in particular inthe case of seeds, furthermore by coating with one or more coats.

Depending on their respective physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, and also ULV cold- and warm-fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents,pressurized liquefied gases and/or solid carriers, optionally with theuse of surface-active agents, that is emulsifiers and/or dispersantsand/or foam formers. If the extender used is water, it is also possibleto employ for example organic solvents as cosolvents. Suitable liquidsolvents are essentially: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample mineral oil fractions, alcohols, such as butanol or glycol aswell as their ethers and esters, ketones, such as acetone, methyl ethylketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents, such as dimethylformamide and dimethyl sulphoxide, and alsowater. Liquefied gaseous extenders or carriers are those liquids whichare gaseous at ambient temperature and at atmospheric pressure, forexample aerosol propellants such as halogenated hydrocarbons and alsobutane, propane, nitrogen and carbon dioxide. As solid carriers thereare suitable: for example ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates. As solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, pumice, marble, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks.As emulsifiers and/or foam formers there are suitable: for examplenon-ionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates. As dispersants there are suitable: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The carboxamides of the formula (I), as such or in their formulations,can also be used as a mixture with known fungicides, bactericides,acaricides, nematicides, or insecticides, for example, to broaden theactivity spectrum or prevent the development of resistance. In manyinstances, synergistic effects are obtained, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of co-components in mixtures are the following compounds:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-5-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; boscalid;bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulphide;capsimycin; captafol; captan; carbendazim; carboxin; carpropamid;carvone; chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al;fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil;furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole;imazalil; imibenconazole; iminoctadine triacetate; iminoctadinetris(albesilate); iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam;metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; propamocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroquilon; pyroxyfur; pyrrolnitrin; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulphur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;2-amino-4-methyl-N-phenyl-5-thiazole-carboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decane-3-amine; sodiumtetrathiocarbonate; and copper salts and preparations, such as Bordeauxmixture; copper hydroxide; copper naphthenate; copper oxychloride;copper sulphate; cufraneb; cuprous oxide; mancopper; oxine-copper.

Bactericides:

Bronopol, dichlorophen, nitrapyrin, nickel dimethyl dithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

1. Acetylcholine Esterase (AChE) Inhibitors

1.1 Carbamates (for example alanycarb, aldicarb, aldoxycarb, allyxycarb,aminocarb, azamethiphos, bendiocarb, benfuracarb, bufencarb, butacarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan,ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb,isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl,pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate,trimethacarb, XMC, xylylcarb)1.2 Organophosphates (for example acephate, azamethiphos, azinphos(-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl),butathiofos, cadusafos, carbophenothion, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos,cyanofenphos, cyanophos, chlorfenvinphos, demeton-5-methyl,demeton-5-methylsulphon, dialifos, diazinon, dichlofenthion,dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos,iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion,malathion, mecarbam, methacrifos, methamidophos, methidathion,mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion(-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos,propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion,pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos,triclorfon, vamidothion)

2. Sodium Channel Modulators/Voltage-Gated Sodium Channel Blockers

2.1 Pyrethroids (for example acrinathrin, allethrin (d-cis-trans,d-trans), beta-cyfluthrin, bifenthrin, bioallethrin,bioallethrin-5-cyclopentyl isomer, bioethanomethrin, biopermethrin,bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin,cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT,deltamethrin, empenthrin (1R isomer), esfenvalerate, etofenprox,fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate,flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox,gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,metofluthrin, permethrin (cis-, trans-), phenothrin (1R trans-isomer),prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin,tetramethrin (1R isomer), tralomethrin, transfluthrin, ZXI 8901,pyrethrins (pyrethrum))2.2 Oxadiazines (for example indoxacarb)

3. Acetylcholine Receptor Agonists/Antagonists

3.1 Chloronicotinyls/neonicotinoids (for example acetamiprid,clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine,thiacloprid, thiamethoxam)3.2 Nicotine, bensultap, cartap

4. Acetylcholine Receptor Modulators

4.1 Spinosyns (for example spinosad)

5. GABA-Gated Chloride Channel Antagonists

5.1 Cyclodiene organochlorines (for example camphechlor, chlordane,endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor5.2 Fiproles (for example acetoprole, ethiprole, fipronil, vaniliprole)

6. Chloride Channel Activators

6.1 Mectins (for example abamectin, avermectin, emamectin, emamectinbenzoate, ivermectin, milbemectin, milbemycin)

7. Juvenile Hormone Mimetics

(for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene,methoprene, pyriproxifen, triprene)

8. Ecdysone Agonists/Disruptors

8.1 Diacylhydrazines (for example chromafenozide, halofenozide,methoxyfenozide, tebufenozide)

9. Chitin Biosynthesis Inhibitors

9.1 Benzoylureas (for example bistrifluoron, chlofluazuron,diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron,lufenuron, novaluron, noviflumuron, penfluoron, teflubenzuron,triflumuron)

9.2 Buprofezin 9.3 Cyromazine 10. Inhibitors of OxidativePhosphorylation, ATP Disruptors 10.1 Diafenthiuron

10.2 Organotins (for example azocyclotin, cyhexatin, fenbutatin oxide)

11. Uncouplers of Oxidative Phosphorylation by Interrupting the H-ProtonGradient

11.1 Pyrroles (for example chlorfenapyr)11.2 Dinitrophenols (for example binapacyrl, dinobuton, dinocap, DNOC)

12. Site-I Electron Transport Inhibitors

12.1 METIs (for example fenazaquin, fenpyroximate, pyrimidifen,pyridaben, tebufenpyrad, tolfenpyrad)

12.2 Hydramethylnone 12.3 Dicofol 13. Site-II Electron TransportInhibitors 13.1 Rotenone 14. Site-III Electron Transport Inhibitors

14.1 Acequinocyl, fluacrypyrim

15. Microbial Disruptors of the Insect Gut Membrane

Bacillus thuringiensis strains

16. Fat Synthesis Inhibitors

16.1 Tetronic acids (for example spirodiclofen, spiromesifen)16.2 Tetramic acids [for example3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl carbonate (also known as: carbonic acid,3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid,cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-ylethyl ester (CAS Reg. No.: 203313-25-1)]

17. Carboxamides

(for example flonicamid)

18. Octopaminergic Agonists

(for example amitraz)

19. Inhibitors of Magnesium-Stimulated ATPase

(for example propargite)

20. Phthalamides

(for exampleN²-[1,1-dimethyl-2-(methylsulphonyl)ethyl]-3-iodo-N¹-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide(CAS Reg. No.: 272451-65-7)

21. Nereistoxin Analogues

(for example thiocyclam hydrogen oxalate, thiosultap-sodium)

22. Biologicals, Hormones or Pheromones

(for example azadirachtin, Bacillus spec., Beauveria spec., codlemone,Metarrhizium spec., Paecilomyces spec., thuringiensin, Verticilliumspec.)23. Active Compounds with Unknown or Unspecific Mechanisms of Action23.1 Fumigants (for example aluminium phosphide, methyl bromide,sulphuryl fluoride)23.2 Selective antifeedants (for example cryolite, flonicamid,pymetrozine)23.3 Mite growth inhibitors (for example clofentezine, etoxazole,hexythiazox)23.4 Amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate,buprofezin, quinomethionate, chlordimeform, chlorobenzilate,chloropicrin, clothiazoben, cycloprene, dicyclanil, fenoxacrim,fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure,hydramethylnone, japonilure, metoxadiazone, petroleum, piperonylbutoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon,tetrasul, triarathene, verbutin, furthermore the compound 3-methylphenylpropylcarbamate (tsumacide Z), the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile(CAS Reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg.No. 185984-60-5) (cf. WO 96/37494, WO 98/25923), and preparations whichcontain insecticidally active plant extracts, nematodes, fungi orviruses.

The active compounds can be employed as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are applied in the customary manner, for example bypouring, spraying, atomizing, broadcasting, dusting, foaming, paintingon and the like. It is furthermore possible to apply the activecompounds by the ultra-low-volume method, or to inject the activecompound preparation or the active compound itself into the soil. Theseed of the plants can also be treated.

When employing the carboxamides of the formula (I) as fungicides, theapplication rates can be varied within a substantial range, depending onthe type of application. In the treatment of plant parts, theapplication rates of active compound are generally between 0.1 and 10000 g/ha, preferably between 10 and 1000 g/ha. For the treatment ofseed, the application rates of active compound are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For treating the soil, the application rates ofactive compound are generally between 0.1 and 10 000 g/ha, preferablybetween 1 and 5000 g/ha.

As already mentioned above, all plants and their parts can be treated inaccordance with the invention. In a preferred embodiment, plant speciesand plant varieties which are found in the wild or are obtained bytraditional biological breeding methods, such as hybridization orprotoplast fusion, and parts of the former are treated. In a furtherpreferred embodiment, transgenic plants and plant varieties which havebeen obtained by recombinant methods, if appropriate in combination withtraditional methods (genetically modified organisms), and their partsare treated. The term “parts” or “parts of plants” or “plant parts” hasbeen illustrated above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are understood as meaning plants with newproperties (“traits”) which have been obtained by conventionalcultivation, by mutagenesis or else by recombinant DNA techniques. Thesemay be cultivars, breeds, biotypes or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, nutrition), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or extensions of the activity spectrum and/or an increase in theactivity of the substances and compositions that can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalinity, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products which exceedthe effects which were actually to be expected are possible.

The preferred transgenic plants or plant cultivars (i.e. those obtainedby genetic engineering) which are to be treated according to theinvention include all plants which, as a result of the recombinantmodification, received genetic material which imparts particularlyadvantageous useful properties (“traits”) to these plants. Examples ofsuch properties are better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalinity, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized in particular are increased defence ofthe plants against insects, arachnids, nematodes, slugs and snails asthe result of toxins formed in the plants, in particular those formed inthe plants by the genetic material from Bacillus thuringiensis (forexample by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits which are alsoparticularly emphasized are the increased defence of plants againstfungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinothricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosates, forexample maize, cotton, soya beans), Liberty Link® (tolerance tophosphinothricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned also include thevarieties sold under the name Clearfield® (for example maize) Of course,these statements also apply to plant cultivars having these genetictraits or genetic traits still to be developed, which cultivars will bedeveloped and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The use of the carboxamides of the formula (I) is illustrated by theexamples below.

USE EXAMPLES Example A Soya Bean Rust Control Test/Spray Application

Preparation of the Test Substances:

5 parts by weight of carboxamide of the formula (I), 142.4 parts byweight of acetone and 7.5 parts by weight of emulsifier (polyoxyethylenealkylphenyl ether) are mixed and adjusted with water to the desiredconcentration.

Test Method:

Soya beans (cultivar: Enrei) were cultivated in plastic containershaving a diameter of 7.5 cm. In each case 3 containers, 6 ml of the testsubstance (preparation as described above) were sprayed onto theseedlings which had reached the 2.3 leaf stage. One day after spraying,the leaves were inoculated with an urediniospore suspension (1×10⁵urediniospores/ml) of Phakopsora pachyrhizi. 14 days after theinoculation, the degree of infection for each container was evaluatedand the efficacy was calculated. The phytotoxicity was also monitored.

TABLE A Soya bean rust control test/spray application Active compoundActive compound application rate in ppm Efficacy in %  (5)

100 80 (33)

100 50 (21)

250 100 90 50  (2)

100 100  (34)

100 93 (35)

100 100  (36)

100 100  (37)

100 50 (38)

100 95 (39)

100 80

1. A method for controlling fungi in soya bean plants comprisingtreating soya bean plants withN-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,wherein said fungi are selected from the group consisting of alternarialeaf spot (Alternaria spec. atrans tenuissima), anthracnose(Colletotrichum gloeosporoides dematium var. truncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostictasojaecola), powdery mildew (Microsphaera diffusa), pyrenochaeta leafspot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and webblight (Rhizoctonia solani), scab (Sphaceloma glycines), stemphyliumleaf blight (Stemphylium botryosum), target spot (Corynesporacassiicola), black root rot (Calonectria crotalariae), charcoal rot(Macrophomina phaseolina), fusarium blight and wilt, root rot, and podand collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusariumsemitectum, Fusarium equiseti), mycoleptodiscus root rot(Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta),pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthephaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma),brown stem rot (Phialophora gregata), pythium rot (Pythiumaphanidermatum, Pythium irregulare, Pythium debaryanum, Pythiummyriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, anddamping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotiniasclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), andthielaviopsis root rot (Thielaviopsis basicola).
 2. The method accordingto claim 1, wherein said fungi are selected from the group consisting ofanthracnose (Colletotrichum gloeosporoides dematium var. truncatum),brown spot (Septoria glycines), cercospora leaf spot and blight(Cercospora kikuchii), drechslera blight (Drechslera glycini), frogeyeleaf spot (Cercospora sojina), powdery mildew (Microsphaera diffusa),rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), targetspot (Corynespora cassiicola), sclerotinia stem decay (Sclerotiniasclerotiorum), and sclerotinia southern blight (Sclerotinia rolfsii). 3.The method according to claim 1, wherein the soya bean plants aretransgenic soya bean plants.
 4. The method according to claim 2, whereinthe soya bean plants are transgenic soya bean plants.
 5. A method ofcontrolling fungi in soya bean plants according to claim 1 comprisingtreating a crop in need of protection from fungi with (a)N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideas the only fungicidally active compound, and (b) optionally, extendersand/or surface-active agents.
 6. The method according to claim 5,wherein the soya bean plants are transgenic soya bean plants.